A revealing new documentary on George Michael highlights both the thrills and perils of massive success.

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Though most listeners know George Michael as the man behind a series of indelible, million-selling pop hits – many of which still play on radio today – the new Showtime documentary Freedom looks to redefine the singer as a warrior in the never-ending battle against exploitative record contracts, an aficionado of soul music and an advocate for stars’ privacy in a world that places cruel pressures on public figures.

Unusually for a posthumous film project, Michael was closely involved with Freedom, set to premiere on Showtime on October 21st. He worked on it until his sudden death on December 25th, 2016, serving as both a narrator and a co-director. In addition, a parade of musical veterans, including Nile Rodgers, Stevie Wonder and Mary J. Blige and supermodels such as Naomi Campbell and Kate Moss pay tribute to Michael’s talents. Here are nine takeaways from the film.

1. Michael always wanted to be a star, even though he knew the demands of stardom could be debilitating.The documentary establishes this central tension immediately as it races through Michael’s career in the duo Wham! “I have a musical ability that as a teenager was powered by this desperate ambition to be famous and be loved and be respected and whatever,” the singer says. “All I wanted at that time was success.

“If I was looking for happiness, this was the wrong road,” he adds. “I still suffered terribly with insecurity about my looks. It goes back to a family background where conceit of any kind was considered an absolute sin, so no one was ever phased about the way they look.”

But the allure of stardom won out – at least in the early Eighties. “I don’t think there’s any way I could’ve controlled my ego enough to stop me from exploring the possibility of being the biggest-selling artist in the world,” Michael admits. “So I went with full gusto into creating a new character, one that would be resonant enough to stand up next to Madonna and [Michael] Jackson and Prince.”

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2. The quality of Michael’s songs was dismissed because they came in cheerful, high-gloss packaging.Michael values one aspect of artistry above all the others. “What do you hope the legacy attached to your name is?” an interviewer asks him late in Freedom. “Great songwriter,” he replies.

He still bristles when considering the reception of his Eighties mega-hits. “I knew how to make these records and how to make them jump out of the radio,” he says. “The idea that just because I was wearing ridiculous shorts would actually stop people from noticing that, when I look back, [is] still kind of stunning.”

3. Michael’s music did a reverse crossover, moving from pop stations to R&B stations and leading to accusations of cultural appropriation.“You heard George Michael on urban stations right after Luther Vandross,” Blige remembers. “His music broke through to everybody.” In an incident that presaged modern critiques of the Grammy Awards and Sam Smith’s no-show at the BET Awards in 2015, Michael later won two American Music Awards in the Soul/R&B category, which traditionally went to black singers who were kept out of competition in the pop categories. “The black male artist works very hard to get his due,” Gladys Knight said in a 1990 interview. “… If [Bobby Brown] could compete in the same category George Michael competes in, that would be a whole ‘nother thing.”

“I won these two awards that were traditionally received by black artists, and I think there was a perception that it had gone too far,” Michael says. “I see their point; I saw their point at the time. I just felt it was sad that white and black people recording together was dancing with the enemy.

“I don’t think there’s any attempt to steal black heritage in what I’m doing,” he adds later. “All I think is happening is I’m trying to make good music.”

4. He got the stardom he craved, and the misery he expected.“I can’t really explain how overwhelming the hysteria can be if there’s only one person to absorb it,” Michael says. “When I was with Andrew [Ridgeley in Wham!], it was so easy to keep one foot in my old life, the life that I knew with him before we were famous. It was easy to keep each other grounded, take the piss out of each other, look at each other and talk about the madness around us. When you can’t do that, suddenly it’s scary. Ten months of that was enough to push me to the edge. I was terribly lonely… The only good part of my day was playing live. When I sang ‘Careless Whisper’ at the end of the American tour, I remember standing there with a tear in my eye thinking I really don’t know if I’ll ever do this again.”

5. Listen Without Prejudice Vol. 1 was simultaneously a chance to hit back against his critics and an homage to the Beatles.Michael suggests he titled his Faith follow-up in response to allegations that he was appropriating black culture. “I suddenly couldn’t get anywhere near black radio, and that was the reason Listen Without Prejudice was called Listen Without Prejudice,” Michael says. “It was me saying, ‘here’s an album that has bits of gospel, bits of R&B, some very white stuff.’ It was time to say, ‘let me be both of these things without having to be one or the other.'”

It was also influenced by a period of infatuation with the Beatles. “I was big into Abbey Road and Revolver,” Michael notes. “I made one record to show how much I loved Lennon [“Praying for Time”], I made another record to show how much I loved McCartney [“Heal the Pain”]. I didn’t dream McCartney would ever sing it [the pair recorded a new version of the song for the greatest hits albums 25]. And actually when he sings it, it sounds like a Paul McCartney record!”

6. Frank Sinatra’s public rebuke to Michael stung.Michael became increasingly public about what he viewed as the deleterious side effects of pop stardom. His record label was not particularly sympathetic; funnily enough, neither was Frank Sinatra, who felt the need to chide Michael in an open letter to the singer. “Come on, George,” Sinatra wrote. “Loosen up. Swing … And no more of that talk about ‘the tragedy of fame.’ The tragedy of fame is when no one shows up and you’re singing to the cleaning lady in some empty joint that hasn’t seen a paying customer since Saint Swithin’s Day.”

Michael hits back in Freedom. “I don’t think [Sinatra] wrote the letter,” the singer says. “I actually believed that was the work of a publicist, not the work of a genius.”

7. Michael’s refusal to be in his own “Freedom ’90” video changed music video culture.In an attempt to protect his sanity, Michael started avoiding traditional promotional duties, refusing to appear in the video for his hit single “Freedom ’90.” Instead, he recruited five models – Naomi Campbell, Linda Evangelista, Tatjana Patitz, Christy Turlington, and Cindy Crawford – to appear in his stead.

“It changed the whole face of how videos were done: The video said everything,” asserts Elton John. “It was genius. And it was a revolutionary thing.”

Andy Stephens, an executive at Michael’s label at the time, remembers the video slightly differently. “That was the lasting memory of the whole video shoot: The cost of the girls and the fees charged on a daily basis. That was pretty groundbreaking!”

8. Michael’s distaste for publicity also led to a prolonged dispute with Sony.“Recording an album and then saying, ‘I’m not going to promote it or I’m not going to market it or I’m not going to participate,’ [is] a serious detriment to an album,” asserts legendary Sony executive Clive Davis. Michael insisted on holding back and, as a result, he believed that Sony under-marketed Listen Without Prejudice in the U.S. The album only landed two Stateside Top Tens versus Faith‘s five.

Michael’s relationship with Sony soured further after the death of the singer’s lover, Anselmo Feleppa, due to complications from AIDS. A grief-stricken Michael could barely write songs. “[Anselmo] was the reason I had the strength to go to battle with Sony,” he explains. “If I could do nothing beneficial as a musician because I cannot even think of a note, maybe I have a chance to do something truly special and change the standard record contract forever.” He took his label to court, accusing the organization of “condemn[ing] him to professional slavery.” “I think to some degree the Sony court case was a perfect way to get rid of all this anger,” he remembers.

Courts tend to favor labels in contract disputes; perhaps predictably, Michael lost his case. “Ultimately, the whole thing was a complete waste of time,” he says in the documentary. “And I regret it to this day.”

9. His favorite George Michael album is Older.Some artists think choosing their best LP is like picking a favorite child. Michael has no such qualms. “Older is my greatest moment,” he asserts, noting that he was finally able to come to terms with the death of Feleppa. “He was my savior – It’s still very hard for me to explain how finding a companion at that stage in my life changed me,” Michael says. He paid homage to Feleppa in the single “Jesus to a Child,” which he describes as “the best, most healing piece of music.”

“It was ‘all systems go’ from that point on,” Michael continues. “For anyone who had a clue about any kind of symbolism, I was coming out. ‘Fast Love’ makes me laugh ’cause it’s about cruising and blunting out that pain with fast love, simple as that. There’s not one track on that album which is not about Anselmo [or] the risk of AIDS. I believe I was destined to feel that particular pain so I could do the ultimate with my music in terms of healing.”